7 Rookie Mistakes That Almost Killed My Business

Let me save you some time and heartache by sharing 7 totally avoidable pitfalls you can sidestep by not. doing. these. things.

Stephanie St.Claire
6 min readMar 3, 2019
photo: Stephanie St.Claire (author)

Today’s advice applies to any person building a career, but this really applies to any person starting a business of their own.

Let me save you some time and heartache by sharing 7 totally avoidable pitfalls you can sidestep by not. doing. these. things. Because I already did them and learned #allthelessons and cried #allthetears.

MISTAKE #1.

I listened to people who had never built a successful business tell me what to do.

HOW I FELL INTO THIS TRAP:

At the beginning of my business, I turned to friend groups and people at networking events to “flesh out” ideas with. I mistakenly thought that pep talks were what I needed instead of straight-up facts and instructions. Many of these people were my friends who were trying to champion me into following my dreams but had totally different dreams themselves (and knew nothing about online business). They were 2 Broadway actors, a political activist, musicians, a corporate speaker, a hotel manager, two bartenders, and a West Elm employee.

WHAT I SHOULD HAVE DONE:

I should’ve sought out seasoned business mentors, signed up for courses in marketing and sales specifically aimed at my field of focus, and registered for coaching with an established business consultant who could help me save time and give me exact instructions on what to do. (Uhhhh, see #2)

MISTAKE #2.

I thought I could do it all on my own without investing any money in help.

HOW I FELL INTO THIS TRAP:

Jazzed up on hyper-optimism, I thought I could figure it out all by myself. Also, I had quit my day job to pursue building my business so money was “tight.” I didn’t realize I would extend the building process by 9 long months trying to learn everything myself and ended up screwing my own money/time economy which led to sad faces 191 days in a row.

WHAT I SHOULD HAVE DONE:

Found the direct route to getting my website up, my client packages organized, and sessions scheduled. Shoulda spent less time on the internet reading blog posts about ‘scalability’ and ‘synergistic SEO.’ I should’ve used a small amount of my modest savings to invest in 2–3 courses, and about a month of mentoring from an experienced online business owner that showed me the basics.

photo: Bonnin Studio on Stocksy

MISTAKE #3.

I did not have a game plan to build my business, step-by-step.

HOW I FELL INTO THIS TRAP:

I didn’t correlate that a logical, simplified roadmap was totally connected with early profitability, financial self-sustainability, and peace in my business. I had misguided beliefs about needing to “learn my way through the trenches” and didn’t think I had the luxury of “slowing down to learn.” But it cost me a TON of time, money, and tears by going it solo it those first 2 years.

WHAT I SHOULD HAVE DONE:

Gotten help. Gotten a blueprint. Stopped cobbling together tips from Shark Tank. Let someone who had done it, who had strategically grown her business, who looked HAPPY for Pete’s sake, who was 5+ years in and still bubbling up with new, innovative ideas for said business, show me how to get mine off the ground so I could have the same.

MISTAKE #4.

I didn’t use a Service Agreement from the very beginning of engagement with my clients.

HOW I FELL INTO THIS TRAP:

I thought it was too formal. I thought I should start work with my clients to “prove” I was worth the money and then slip them the contract a month or two into our work. DUMB! I know! And then I proceeded to have several “client misunderstandings” about last-minute cancellations, late payments, my business hours not including Christmas Day, expectations of what they were getting exactly, etc.

WHAT I SHOULD HAVE DONE:

Had a beautifully written Service Agreement from day one that showed the client I cared about them and our business relationship, and I had taken responsibility for putting it all out in writing for them to peruse and agree to. I would’ve come across as a professional consultant who had high expectations for our client-consultant relationship.

photo: Bonnin Studio on Stocksy

MISTAKE #5.

I waited 2 years to create evergreen products that would bring in multiple streams of income.

HOW I FELL INTO THIS TRAP:

I felt overwhelmed by the technology of creating even a small online course, and also had a skewed grandiosity about the whole thing — like it had to be my Magnum Opus or something — instead of just smart, helpful, and succinct.

I was a coach and writer who just wanted to coach and write all day and not deal with technology and sales funnels.

I didn’t get it.

WHAT I SHOULD HAVE DONE:

Created three ways to make money with my business instead of relying on consulting sessions alone, because let me tell you that the gut-wrenching vagaries of euphoria and despair are REAL MAN, when you make $4,000 one month and $100 the next month even though you worked your butt off both months with equal amounts of “passion.”

The solution is quite easy: Create a private consultancy, create a community workshop, and create a few downloadable products that make money for you 24/7. That way your months look more like: $7,200.00, $8,500.00, $9,800.00.

MISTAKE #6.

I put more emphasis on learning design than learning how to close sales.

HOW I FELL INTO THIS TRAP:

Design is pretty. Sales are scary.

WHAT I SHOULD HAVE DONE:

Found the leaders I respect already and study them. In other words, the “online marketing gurus” and their accompanying sales stratagem aren’t always the best resources for legit business knowledge. The first thing I did was enroll in a sales and negotiation course at NYU. I read books and articles about business people I admire and took COPIOUS NOTES about how they presented themselves and their work in the world. My faves: Diane von Furstenberg, Ray Dalio, Kenneth Langone, Sara Blakely, Barbara Corcoran, Terry Gross, Steven Pressfield, Mike Michaelowicz, and okay, yes, Gary Vaynerchuk.

MISTAKE #7.

I spent more time building my social media following than my email list.

HOW I FELL INTO THIS TRAP:

I didn’t realize that social media is where you build a lovely community who will give you great feedback and spread the word about you, but social media fans DO NOT = paying clients. I don’t know if anyone really knew that in 2012? because we were all trying to get as many FB fans as we could. Social proof is a nice flex, but it doesn’t keep the lights on.

WHAT I SHOULD HAVE DONE:

Written to my small, intimate group of email subscribers FROM DAY ONE and nurtured the heck out of that community to foster trust and relationship. Once I started doing that (about 18 months into the business) I had subscribers soliciting consulting from me — which made booking out the client roster quite easy.

I’ve written more about this in 11 Things I Wish I Knew When I Started My Business:

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Stephanie St.Claire is a writer and personal advisor based in Orange County, California. Her work has been featured in The Huffington Post, Fast Company, Inc., Thought Catalogue, Greatist, Citizens of Culture, Mind Body Green and has been named one of Medium’s Top 100 Writers.

website: stephaniestclaire.com
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Stephanie St.Claire

Writer. Reader. Lover of the Oxford comma. Writing for Medium since 2013. Find me at stephaniestclaire.com